The history of Emanuel Wynn or Emanuel Wynne is very limited and not much is known of his life before piracy other than his penchant for plundering English and Spanish ships in the seventeenth century. His patrol area changed from first along the coast of the New World and later where others had gone and that was the Caribbean. Emanuel Wynn’s life, much like that of many pirates, is a puzzle with many missing pieces. Historical records on pirates are often scarce and unreliable, as they were outlaws living on the fringes of society. His claim to fame came not for his piracy but rather for being accredited as the first to fly the Jolly Roger image. This account of the encounter was described by Captain John Cranby of the Royal Navy the interaction was brief eventually, Wynn was able to escape because reinforcement delayed the attempt to capture him.

No further details of his mention after that can be located as to life after that or possible demise later in life. The voyages of Emanuel Wynn remain a topic of great interest among historians and piracy enthusiasts. Emanuel Wynn was not just a pirate but a strategist. He employed various tactics to outmaneuver his targets. While not as famous as some of his contemporaries, Emanuel Wynn’s contributions to pirate lore are undeniable His flag is a variant of today's most famous pirate flag – crossbones motif, but with an addition of an hourglass which represented that pirate prey’s time is up. Another possible explanation of an hourglass motif is that prey can only evade death by surrendering immediately.